GB994215A - Isophthalic acid derivatives and process for preparing same - Google Patents

Isophthalic acid derivatives and process for preparing same

Info

Publication number
GB994215A
GB994215A GB29941/61A GB2994161A GB994215A GB 994215 A GB994215 A GB 994215A GB 29941/61 A GB29941/61 A GB 29941/61A GB 2994161 A GB2994161 A GB 2994161A GB 994215 A GB994215 A GB 994215A
Authority
GB
United Kingdom
Prior art keywords
acid
amino
lower alkyl
ester
nitro
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
GB29941/61A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Mallinckrodt Chemical Works
Original Assignee
Mallinckrodt Chemical Works
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from US119287A external-priority patent/US3145197A/en
Application filed by Mallinckrodt Chemical Works filed Critical Mallinckrodt Chemical Works
Publication of GB994215A publication Critical patent/GB994215A/en
Expired legal-status Critical Current

Links

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
    • A61K31/19—Carboxylic acids, e.g. valproic acid
    • A61K31/195—Carboxylic acids, e.g. valproic acid having an amino group
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K49/00—Preparations for testing in vivo
    • A61K49/04—X-ray contrast preparations
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
    • C07C205/49—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups
    • C07C205/57—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/12—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by halogen atoms or by nitro or nitroso groups

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Epidemiology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Medicinal Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

The invention comprises compounds of general formula <FORM:0994215/C2/1> wherein R1 and R2 are independently hydrogen atoms or lower (i.e. 1-6 C) alkyl groups, and R3 is a hydrogen atom or a lower alkanoyl group; and the non-toxic pharmaceutically acceptable lower alkyl esters and salts thereof; and their preparation by processes which broadly comprise (1) obtaining compounds wherein R3 is alkanoyl by acylation of the corresponding amino compounds; (2) reacting a 5-nitro-isophthalic acid monolower alkyl ester with ammonium hydroxide or a lower alkylamine to form the corresponding salt of a 5 - nitro - isophthalic acid monoamide, converting this to the acid, reducing the nitro group to 5-amino, and iodinating the product; (3) reacting a 3-carboalkoxy-5-nitrobenzoyl halide with ammonium hydroxide or a mono- or di-lower alkyl amine to form the corresponding lower alkyl ester of a 5-nitro-isophthalic acid monoamide, hydrolysing this to the acid, reducing the nitro group to 5-amino, and iodinating the product; (4) reacting a 5-amino-isophthalic acid mono-lower alkyl ester with ammonium hydroxide or a mono- or di-lower alkylamine, forming the isophthalamic acid derivative and iodinating this; (5) obtaining the lower alkyl esters by reacting a salts of the acids with an alkylating agent in a substantially anhydrous solvent. Other processes mentioned for preparing intermediates are reaction of 5-aminoisophthalic acid monoesters with thionyl chloride, the 3-carbalkoxy - 5 - thionylaminobenzoyl chloride formed yielding, with ammonium hydroxide or a mono- or die alkylamine, a 5-aminoisophthalamic acid. 5 - Nitroisophthalic acid monomethyl ester is prepared by partial hydrolysis of the dimethyl ester, and with phosphorus pentachloride yields 3 - chloroformyl - 5 - nitrobenzoic acid methyl ester.ALSO:Compositions for use as X-ray contrast media contain 5 - amino - triiodoisophthalamic acid derivatives of general formula <FORM:0994215/A5-A6/1> wherein R1 and R2 are independently hydrogen atoms or lower (i.e. 1-6 C) alkyl groups and R3 is a hydrogen atom or a lower alkanoyl group and their nontoxic pharmaceutically acceptable lower alkyl esters and their salts (e.g. sodium and N-methyl glucamine salts); solutions are exemplified.
GB29941/61A 1960-08-25 1961-08-18 Isophthalic acid derivatives and process for preparing same Expired GB994215A (en)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US5178660A 1960-08-25 1960-08-25
US119287A US3145197A (en) 1961-06-26 1961-06-26 5-acetamido-nu-alkyl-2, 4, 6-trhodoiso-phthalamic acid compounds
US12138861A 1961-07-03 1961-07-03
US12537361A 1961-07-20 1961-07-20

Publications (1)

Publication Number Publication Date
GB994215A true GB994215A (en) 1965-06-02

Family

ID=27489435

Family Applications (1)

Application Number Title Priority Date Filing Date
GB29941/61A Expired GB994215A (en) 1960-08-25 1961-08-18 Isophthalic acid derivatives and process for preparing same

Country Status (6)

Country Link
BE (1) BE607551A (en)
CH (1) CH424751A (en)
DE (1) DE1443297C3 (en)
ES (1) ES270024A1 (en)
FR (1) FR1589M (en)
GB (1) GB994215A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP4801661B2 (en) * 2005-03-18 2011-10-26 マナック株式会社 Method for acetylating 5-amino-2,4,6-triiodoisophthalic acid derivative

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP4801661B2 (en) * 2005-03-18 2011-10-26 マナック株式会社 Method for acetylating 5-amino-2,4,6-triiodoisophthalic acid derivative

Also Published As

Publication number Publication date
ES270024A1 (en) 1962-01-01
DE1443297A1 (en) 1972-01-13
FR1589M (en) 1962-11-26
BE607551A (en) 1962-02-26
DE1443297C3 (en) 1975-04-17
DE1443297B2 (en) 1974-08-29
CH424751A (en) 1966-11-30

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